Practical chemoselective aromatic substitution: the synthesis of -(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of -phenylbenzenesulfonamide
A novel route involving the metal-promoted tandem nitration and halogenation of N -phenylbenzenesulfonamide to synthesize N -(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed. The method shows highly practical chemoselective and functional group compatibility. In addition, it e...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2022-07, Vol.2 (27), p.5444-5451 |
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| container_issue | 27 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Yu, Xiao Zhu, Wenjing Liu, Hongyan Liu, Yi Li, Hongshuang Han, Junfen Duan, Guiyun Bai, Zhushuang Zhang, Pengfei Xia, Chengcai |
| description | A novel route involving the metal-promoted tandem nitration and halogenation of
N
-phenylbenzenesulfonamide to synthesize
N
-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed. The method shows highly practical chemoselective and functional group compatibility. In addition, it employs insensitive and inexpensive Cu(NO
3
)
2
3H
2
O, Fe(NO
3
)
3
9H
2
O, and NH
4
NO
3
as the nitration reagents, and it provides a direct approach for the preparation of 4-halo-2-nitroaniline, which is a crucial intermediate for the synthesis of benzimidazoles and quinoxaline derivatives.
A novel route involving the metal-promoted tandem nitration and halogenation of
N
-phenylbenzenesulfonamide to synthesize
N
-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed. |
| doi_str_mv | 10.1039/d2ob01028c |
| format | Article |
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N
-phenylbenzenesulfonamide to synthesize
N
-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed. The method shows highly practical chemoselective and functional group compatibility. In addition, it employs insensitive and inexpensive Cu(NO
3
)
2
3H
2
O, Fe(NO
3
)
3
9H
2
O, and NH
4
NO
3
as the nitration reagents, and it provides a direct approach for the preparation of 4-halo-2-nitroaniline, which is a crucial intermediate for the synthesis of benzimidazoles and quinoxaline derivatives.
A novel route involving the metal-promoted tandem nitration and halogenation of
N
-phenylbenzenesulfonamide to synthesize
N
-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d2ob01028c</identifier><ispartof>Organic & biomolecular chemistry, 2022-07, Vol.2 (27), p.5444-5451</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Yu, Xiao</creatorcontrib><creatorcontrib>Zhu, Wenjing</creatorcontrib><creatorcontrib>Liu, Hongyan</creatorcontrib><creatorcontrib>Liu, Yi</creatorcontrib><creatorcontrib>Li, Hongshuang</creatorcontrib><creatorcontrib>Han, Junfen</creatorcontrib><creatorcontrib>Duan, Guiyun</creatorcontrib><creatorcontrib>Bai, Zhushuang</creatorcontrib><creatorcontrib>Zhang, Pengfei</creatorcontrib><creatorcontrib>Xia, Chengcai</creatorcontrib><title>Practical chemoselective aromatic substitution: the synthesis of -(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of -phenylbenzenesulfonamide</title><title>Organic & biomolecular chemistry</title><description>A novel route involving the metal-promoted tandem nitration and halogenation of
N
-phenylbenzenesulfonamide to synthesize
N
-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed. The method shows highly practical chemoselective and functional group compatibility. In addition, it employs insensitive and inexpensive Cu(NO
3
)
2
3H
2
O, Fe(NO
3
)
3
9H
2
O, and NH
4
NO
3
as the nitration reagents, and it provides a direct approach for the preparation of 4-halo-2-nitroaniline, which is a crucial intermediate for the synthesis of benzimidazoles and quinoxaline derivatives.
A novel route involving the metal-promoted tandem nitration and halogenation of
N
-phenylbenzenesulfonamide to synthesize
N
-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFkLFOxDAQRC0EEsdBQ4_kEgofdhIIoUWcKCnoT46zPhs565PXQQpfxueRcAgKCqrZ2dG8Yhg7V3KlZNlcd0VspZLFnTlgC1XVtZA3ZXP4cxfymJ0QvUqpmvq2WrCP56RN9kYHbhz0kSDA5N-A6xR7PSWchpayz0P2Ee95dsBpxEnIE4-Wi8tKOB2iKAT6nOLOAY7hqgV8BwQago2oe9_BVE1x2LovBFjrjQfMfC7pmc01dnwmbQH3j5m-x_2lnbIjqwPB2bcu2cX68eXhSSQym13yvU7j5neO8r_8EzBcabI</recordid><startdate>20220713</startdate><enddate>20220713</enddate><creator>Yu, Xiao</creator><creator>Zhu, Wenjing</creator><creator>Liu, Hongyan</creator><creator>Liu, Yi</creator><creator>Li, Hongshuang</creator><creator>Han, Junfen</creator><creator>Duan, Guiyun</creator><creator>Bai, Zhushuang</creator><creator>Zhang, Pengfei</creator><creator>Xia, Chengcai</creator><scope/></search><sort><creationdate>20220713</creationdate><title>Practical chemoselective aromatic substitution: the synthesis of -(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of -phenylbenzenesulfonamide</title><author>Yu, Xiao ; Zhu, Wenjing ; Liu, Hongyan ; Liu, Yi ; Li, Hongshuang ; Han, Junfen ; Duan, Guiyun ; Bai, Zhushuang ; Zhang, Pengfei ; Xia, Chengcai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_d2ob01028c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><creationdate>2022</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yu, Xiao</creatorcontrib><creatorcontrib>Zhu, Wenjing</creatorcontrib><creatorcontrib>Liu, Hongyan</creatorcontrib><creatorcontrib>Liu, Yi</creatorcontrib><creatorcontrib>Li, Hongshuang</creatorcontrib><creatorcontrib>Han, Junfen</creatorcontrib><creatorcontrib>Duan, Guiyun</creatorcontrib><creatorcontrib>Bai, Zhushuang</creatorcontrib><creatorcontrib>Zhang, Pengfei</creatorcontrib><creatorcontrib>Xia, Chengcai</creatorcontrib><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yu, Xiao</au><au>Zhu, Wenjing</au><au>Liu, Hongyan</au><au>Liu, Yi</au><au>Li, Hongshuang</au><au>Han, Junfen</au><au>Duan, Guiyun</au><au>Bai, Zhushuang</au><au>Zhang, Pengfei</au><au>Xia, Chengcai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Practical chemoselective aromatic substitution: the synthesis of -(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of -phenylbenzenesulfonamide</atitle><jtitle>Organic & biomolecular chemistry</jtitle><date>2022-07-13</date><risdate>2022</risdate><volume>2</volume><issue>27</issue><spage>5444</spage><epage>5451</epage><pages>5444-5451</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A novel route involving the metal-promoted tandem nitration and halogenation of
N
-phenylbenzenesulfonamide to synthesize
N
-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed. The method shows highly practical chemoselective and functional group compatibility. In addition, it employs insensitive and inexpensive Cu(NO
3
)
2
3H
2
O, Fe(NO
3
)
3
9H
2
O, and NH
4
NO
3
as the nitration reagents, and it provides a direct approach for the preparation of 4-halo-2-nitroaniline, which is a crucial intermediate for the synthesis of benzimidazoles and quinoxaline derivatives.
A novel route involving the metal-promoted tandem nitration and halogenation of
N
-phenylbenzenesulfonamide to synthesize
N
-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed.</abstract><doi>10.1039/d2ob01028c</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2022-07, Vol.2 (27), p.5444-5451 |
| issn | 1477-0520 1477-0539 |
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| recordid | cdi_rsc_primary_d2ob01028c |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Practical chemoselective aromatic substitution: the synthesis of -(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of -phenylbenzenesulfonamide |
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